The dew point is the temperature at which the air becomes saturated with water vapor. This water vapor is the condensation, or dew, that begins to form when the relative humidity reaches 100%.

The dew point also explains why landlocked cities like Las Vegas and New Delhi in the summer feel markedly different from cities near bodies of water like Jacksonville or Manila, even with the temperature being the same. Warm air can hold more water vapor, and the stifling stickiness we experience is the dew point at work.

I’d like to posit that a related phenomenon is at work when we engage in challenging interpersonal communication. When we take the time to deliver feedback with thoughtfulness and care, its impact is vastly different from communication that takes place under conditions of frustration and resentment.

The good news is that we exert far more influence over the ambient emotional temperature than we do the weather outside.

When we do the hard work of processing our emotions beforehand and communicating from a place of generosity, the emotional dew point reaches a point where the recipient can experience the substance of our message rather than the suffocating negative emotions we’re radiating.

One of the pitfalls of people-pleasing is that none of the people, over the long term, are pleased, least of all, you. We lose a part of ourselves each time.

Short-term thinking invites us to say yes in a way that reduces short-term discomfort, but this only accelerates our journey to an untenable destination.

The alternative is, of course, getting clear with ourselves (and then others) about the rules of engagement, even and especially when that means having an uncomfortable conversation up front.

“Boundaries are the distance at which I can love you and me simultaneously.”
—Prentis Hemphill

Oak Bluffs is an idyllic resort town on Martha’s Vineyard that has held a unique place in black history since the late 1800s. During segregation, it was one of the few resort communities where black families could vacation freely alongside white families. It still serves as an important oasis and gathering place for (wealthy) black families and professionals, with many rental properties booked years in advance by its loyal patrons.

Ralph Lauren honored this rich history last week with a collection in partnership with Morehouse and Spelman Colleges. As a part of the campaign, they released a documentary titled A Portrait of the American Dream: Oak Bluffs. Enjoy.

The people who advance most quickly in new roles aren’t necessarily the most ambitious, qualified, or hard-working—they’re the ones who arrive with a clear idea of what they’re looking to learn, contribute, and accomplish.

Rapid advancement might not be your goal, but incredible things can happen when you hold yourself to a compressed timeline. And even if your goals shift over time (they will), the point of creating them is the effort it takes to define them in the first place.

A trap I see many brilliant folks falling into is treating their job as a cog in the organization’s machinery, rather than a vehicle by which to accelerate their professional trajectory. When we contort ourselves to fit into a machine, it often starches out the thing that makes us special and differentiated.

The reality is that the best opportunities benefit from (and encourage) the things not listed in the job description, and these unique contributions can paradoxically stem from what you’re bringing rather than what you’re asked to do.

This doesn’t mean that we can ignore our responsibilities—executing on those is table stakes—but we can also earn the privilege of contributing more.

And one of the many benefits of knowing what you’re looking to get out of an experience is the clarity that informs when it’s time to make a change.

I’ve always looked forward to big moves and new beginnings, in particular as catalysts for personal growth and development. When I moved to Buenos Aires in 2013, my first order of business was to shave my head and see how I looked bald. The good news is that I could pull off the look, but why did I have to wait for a 5,000-mile flight to fire up the clippers?

When I started summer basketball camp in elementary school, none of my teammates were there. And for whatever reason, I felt free to inhabit a different and better athletic identity, and quickly established myself as one of the best players. Wasn’t that already available to me?

We put off becoming the person we might be by saving the effort for “one day” in the future. But just as January 1st is an entirely arbitrary date on which to begin resolutions, we don’t even have to wait for tomorrow to become the person we want to be.

Start today.

One of my first high-stakes facilitation assignments was an engagement outside of Santa Barbara, California. I was facilitating a Leadership Lab, with “My Beautiful Story,” an activity I created, serving as the centerpiece. The client had rented a stunning mansion for the offsite and all of their high-potential leaders were invited.

At the time, ReadySet had a small office in what used to be a mall that had been converted into a coworking space. I was meeting with my CEO about the engagement before I flew out, which I expected to be a formality. The meeting, as it turned out, was not a formality.

She asked me to review my opening remarks and share how I intended to introduce the activity. And not just voice over my plan, she wanted me to stand up and role-play my opening remarks for her as if there was an audience present.

I clicked my heels, hoping to find myself in Kansas, or at least somewhere other than that meeting, but when I opened my eyes again, five excruciating seconds had passed, and I was still very much sitting across from my CEO in Oakland.

I stood up and offered a miserable, stuttering first attempt. Y-Vonne mercifully stopped me and calmly said, “Start over.” I looked down and still didn’t see any sign of a yellow brick road, so I took a breath and tried again.

She interrupted my second attempt by offering better phrasing which I graciously received while feeling confident that I could face a firing squad with more equanimity.

But on we went like this for what felt like an hour, and by the end of the exercise, I felt confident and prepared. I felt better aligned with how the session and the activity fit into the broader arc of the client’s programming, and I felt better prepared to showcase the growing canon of dynamic organizational interventions our firm was developing.

The preparation paid off, and we continued working with the client for five years.

The experience showed me the power of combining the power of preparation the with art of improvisation. Many of us who facilitate, speak, and perform in front of audiences have to adapt to things in the moment, but it’s the practice behind the scenes that makes the performance look effortless.

Every time I publish a piece of writing here, I feel both relief and regret. Relief that for another day, I showed up, published something that I believe, and offered a bit of myself to be judged by friends and strangers alike. I also regret not publishing something better, longer, and clearer.

But that’s a tradeoff I’m willing to make, because the point of the writing practice isn’t to change your life right now—it’s to change mine. I’m having a conversation with myself, out loud, and bringing others along for the ride.

Will the nature of what I share change over time? Of course. But for now, I’m embracing the imperfection.

In 2019, while working for ReadySet, I got an email offering us a sponsorship opportunity for From Day One’s upcoming event in San Francisco. ReadySet was based in Oakland, and we were eager to showcase our work, but we weren’t in a place to invest in the sponsorship with the ROI being unclear.

But where there’s a Will, there’s a way.

My friend Maurice was a DEI director with a substantial budget, so I pitched him on sponsoring the breakout and co-facilitating it with me. He was on board.

The breakout was well-received and well-attended—people were standing in the doorway and sitting on the floor in the aisle which of course wasn’t a fire hazard. Afterwards, Nick, the co-founder of the conference, asked me if I would deliver that same content at their upcoming event in Brooklyn. I agreed.

Nearly 200 people attended the Brooklyn session. The content landed, and so did my jokes. A colleague in attendance took me to lunch afterwards and tried to poach me. Something was happening.

I formalized the partnership with From Day One, and we took the show on the road. I served as the closing keynote speaker for FD1 conferences in Atlanta, Boston, Dallas, Los Angeles, Miami, Philadelphia, and Seattle. I leveled up and business grew. The ROI was clear.

And then 7,000 miles away, something weird happened in China, and I stopped traveling, just like everyone else. Things got quiet for a few months, but after a police officer in Minneapolis knelt on George Floyd’s neck with the world watching, things got decidedly less quiet.

The seeds planted in those sessions across the nation bore fruit, and business exploded. We had more work than we knew what to do with, and I delivered two to three virtual workshops a day for weeks. Maybe months.

Looking back, the From Day One partnership was one of the most economically and professionally rewarding relationships of the past decade. It altered my professional trajectory in ways I’m still benefiting from. What a ride.

I had reached a career pinnacle—making partner at a firm I helped build—but I had never felt more adrift and unmoored. Two of my super-powers are facilitation and business development, and I have a history of combining these passions to great success. But these things weren’t my priorities at the time.

The challenge is that the company needed a “strategic executive” in the Head of Growth seat to which I had been promoted. I spent months trying to figure out what that meant in practice. It felt like putting business words about the future into documents and decks, and what I really wanted to do was close business and perform The Willie Jackson Show on stages every week. Tensions grew.

When I brought the issue to my executive coach, he listened patiently while I spent our call tying myself in knots. As the call ended, he issued me a simple challenge. He said, “If you’re going to be there, act like you want to be there.”

It was comical in its simplicity, but it completely interrupted my unproductive rumination. The following week, I hijacked a meeting with my CEO and COO with an insight that Stevie Wonder clearly beheld: this isn’t working.

The response was validating and relieving: “We agree, and we’re so glad you said something before we did.”

***

Exactly one year ago today, I submitted my resignation, and the process couldn’t have been more supportive and straightforward. I’ve learned and grown so much in the past year, in ways I’m still noticing.

Living in alignment with your truth isn’t always convenient or easy, but it’s worth it.